Abstract
C14H10Cl2N2O2, triclinic,
The molecular structure is shown in the figure. Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Data collection and handling.
| Crystal: | Yellow block |
| Size: | 0.41 × 0.38 × 0.33 mm |
| Wavelength: | Mo Kα radiation (0.71073 Å) |
| μ: | 0.50 mm−1 |
| Diffractometer, scan mode: | Bruker APEX-II, φ and ω |
| θ max, completeness: | 25.0°, >99% |
| N(hkl)measured, N(hkl)unique, R int: | 3150, 1160, 0.013 |
| Criterion for I obs, N(hkl)gt: | I obs > 2 σ(I obs), 1028 |
| N(param)refined: | 92 |
| Programs: | Bruker [1], SHELX [2, 3] |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
| Atom | x | y | z | U iso*/U eq |
|---|---|---|---|---|
| C1 | 0.4596 (3) | 0.3200 (2) | 0.3872 (2) | 0.0407 (4) |
| C2 | 0.6783 (3) | 0.2419 (2) | 0.4198 (2) | 0.0445 (4) |
| C3 | 0.7262 (3) | 0.1472 (3) | 0.5905 (2) | 0.0510 (4) |
| H3 | 0.871152 | 0.092328 | 0.611733 | 0.061* |
| C4 | 0.5626 (3) | 0.1333 (2) | 0.7286 (2) | 0.0503 (4) |
| H4 | 0.596520 | 0.070425 | 0.843404 | 0.060* |
| C5 | 0.3478 (3) | 0.2124 (2) | 0.6973 (2) | 0.0459 (4) |
| C6 | 0.2954 (3) | 0.3033 (2) | 0.5293 (2) | 0.0455 (4) |
| H6 | 0.149081 | 0.354310 | 0.509709 | 0.055* |
| C7 | 0.3993 (3) | 0.4212 (2) | 0.2121 (2) | 0.0446 (4) |
| H7 | 0.251233 | 0.468702 | 0.196384 | 0.053* |
| Cl1 | 0.14214 (8) | 0.19598 (8) | 0.87486 (6) | 0.0676 (2) |
| N1 | 0.5439 (2) | 0.4472 (2) | 0.07842 (17) | 0.0469 (4) |
| O1 | 0.8469 (2) | 0.2561 (2) | 0.28996 (16) | 0.0632 (4) |
| H1 | 0.798238 | 0.308576 | 0.194068 | 0.095* |
Source of materials
5-Chlorosalicylaldehyde (1.56 g, 10 mmol), hydrazine hydrate (0.25 g, 5 mmol) and ethanol (30 mL) were heated and stirred at 353 K for 8 h. Then the solvent was concentrated and filtered. The crude product was recrystallized from ethanol to afford yellow crystals (1.31 g, yield 85%).
Experimental details
All hydrogen atoms were identified in difference Fourier syntheses. The U iso values of the hydrogen atoms of phenolic hydroxyl groups were set to 1.5U eq (C) and the U iso values of all other hydrogen atoms were set to 1.2U eq (C).
Comment
Schiff bases are a class of compounds containing the imino group –C=N–, which have important chemical and biological properties [4, 5]. Schiif bases may have antibacterial, anti-inflammatory, anti-tumor and anti-viral biological activities [6, 7]. Salicylaldehyde Schiff bases are an important class of chemical analysis reagents and organic ligands, and they are widely used in fluorescent probes [8]. We have also reported some Schiff bases of salicylaldehyde [9, 10].
The asymmetric unit of the title structure contains one half of the title molecule (see the figure). It can be clearly seen in the structure that the intra molecular hydrogen bonds are formed between the hydrogen atom of the phenolic hydroxyl group and the nitrogen atom of the imine. The molecule is in the trans configuration at the C(7)–N(1) double bond (1.273(3) Å). The bond angle of N(1)–C(7)–C(1) is 121.57(19)°. The geometric parameters of the title structure are all in the expected ranges [11].
Funding source: Natural Science Foundation of Hunan Province of China
Award Identifier / Grant number: 2021JJ30291
Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China
Award Identifier / Grant number: [2021]197-3585
Funding source: Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering
Award Identifier / Grant number: 2021
Funding source: Yongzhou Guiding Science and Technology Plan Project
Award Identifier / Grant number: 2021
Funding source: the Construct Program of Applied Characteristic Discipline in Hunan University of Science and Engineering
Funding source: the Scientific Research Fund of Hunan Provincial Education Department
Award Identifier / Grant number: 21A0518, 21C0691
-
Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
-
Research funding: This work was financially supported by Natural Science Foundation of Hunan Province of China (2021JJ30291), the Scientific Research Fund of Hunan Provincial Education Department (21A0518, 21C0691), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan Province of China ([2021]197-3585), Undergraduate Training Program for Innovation and Entrepreneurship of Hunan University of Science and Engineering (2021), Yongzhou Guiding Science and Technology Plan Project (2021), the construct program of applied characteristic discipline in Hunan University of Science and Engineering.
-
Conflict of interest statement: The authors declare no conflicts of interest regarding this article.
References
1. Bruker. APEX3, SAINT-Plus, XPREP; Bruker AXS Inc.: Madison, Wisconsin, USA, 2016.Suche in Google Scholar
2. Sheldrick, G. M. SHELXTL – integrated space-group and crystal-structure determination. Acta Crystallogr. 2015, A71, 3–8; https://doi.org/10.1107/s2053273314026370.Suche in Google Scholar PubMed PubMed Central
3. Sheldrick, G. M. Crystal structure refinement with SHELXL. Acta Crystallogr. 2015, C71, 3–8; https://doi.org/10.1107/s2053229614024218.Suche in Google Scholar
4. Kumari, S., Chauhan, G. New cellulose-lysine Schiff-base-based sensor- adsorbent for mercury ions. ACS Appl. Mater. Interfaces 2014, 6, 5908–5917; https://doi.org/10.1021/am500820n.Suche in Google Scholar PubMed
5. Sidi, B. M. V., Elemine, B., Aliyenne, A., Hadou, A., Daich, A., Othman, M., Lawson, A. M. Highly enantioselective semisynthesis of (+)/(−)-Gossypol Schiff base derivatives from ground plant material. J. Nat. Prod. 2019, 82, 1779–1790; https://doi.org/10.1021/acs.jnatprod.8b01045.Suche in Google Scholar PubMed
6. Kolodziej, B., Morawiak, M., Schilf, W., Kamieński, B. Structure investigations of Schiff bases derived from 3-amino-1H-1,2,4-triazole. J. Mol. Struct. 2019, 1184, 207–218.10.1016/j.molstruc.2019.02.027Suche in Google Scholar
7. Bigyan, R. J., Jubaraj, B. B. Recent progress in Schiff bases in detections of fluoride ions. Dyes Pigments 2021, 194, 109575.10.1016/j.dyepig.2021.109575Suche in Google Scholar
8. Singh, G., Sindhu, J., Manisha Kumar, V., Sharma, V., Sharma, S. K., Mehta, S. K., Mahnashi, M. H., Umar, A., Kataria, R. Development of an off-on selective fluorescent sensor for the detection of Fe3+ ions based on Schiff base and its Hirshfeld surface and DFT studies. J. Mol. Liq. 2019, 296, 111814; https://doi.org/10.1016/j.molliq.2019.111814.Suche in Google Scholar
9. Li, Z.-Y., Jia, G.-K., Yuan, L., Bai, P.-F., He, H., Zhou, Q. Syntheses, crystal structures and biological activities of three new Schiff bases derived from substituted salicylaldehyde and tris base. Chin. J. Struct. Chem. 2017, 36, 1797–1802.Suche in Google Scholar
10. Yuan, L., Li, Y.-D., Fan, X., Li, Z.-Y. The crystal structure of (E)- 2-((tert-butylimino)methyl)-4-chlorophenol, C11H14ClNO. Z. Kristallogr. N. Cryst. Struct. 2021, 236, 1317–1318; https://doi.org/10.1515/ncrs-2021-0323.Suche in Google Scholar
11. Safin, D. A., Robeyns, K., Garcia, Y. Solid-state thermo- and photochromism in N,N′-bis(5-X-salicylidene)diamines (X = H, Br). RSC Adv. 2012, 2, 11379–11388. https://doi.org/10.1039/c2ra21631k.Suche in Google Scholar
© 2021 Xu Fan et al., published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of {2,2′-{cyclohexane-1,2-diylbis[(azanylylidene)methylylidene]}bis(2,4-dibromophenolato)-κ4 N,N′,O,O′}copper(II) ─ diethylformamide (1/1), C23H23Br4CuN3O3
- The crystal structure of 2-(2-methyl-6-phenyl-4H-pyran-4-ylidene)-1H-indene-1,3(2H)-dione, C21H14O3
- Crystal structure of bis((1-methylbenzimidazol-2-yl)methyl)amine, C18H19N5
- Crystal structure of (E)-N′-(1-(2-hydroxy-4-methoxyphenyl)ethylidene) isonicotinohydrazide, C15H15N3O3
- Crystal structure of 2-((4-phenyl-5-(pyridin-4-yl)-4H-1,2,4-triazol-3-yl)thio)acetonitrile, C15H11N5S
- The crystal structure of 2,2′-((1E,1′E)-hydrazine-1,2-diylidenebis(methaneylylidene))bis(4-chlorophenol), C14H10Cl2N2O2
- Dichlorido-{2,6-bis(4,5-dihydro-1H-pyrazol-3-yl)pyridine-κ3 N,N′,N″}zinc(II), C11H9C12N5Zn
- The crystal structure of dichlorido-(2-((4-phenyl-2H-1,2,3-triazol-2-yl)methyl)pyridine-κ2N,N′)palladium(II), C14H12Cl2N4Pd
- The crystal structure of 1-(N1-benzyl-2-methyl-4-nitro-imidazol-5-yl)-4-(prop-2-yn-1-yl) piperazine, C18H21N5O2
- Crystal structure of (μ4-(1,2,4,5-tetra(1,2,4-triazol-1-ylmethyl)-benzene-κ4N:N1:N2:N3)disilver(I) diperchlorate
- The crystal structure of 1-(2-bromoethane)-4-amine-3,5-dinitropyrazole, C5H6Br1N5O4
- Crystal structure of (E)-1-(4-benzyl-3,5-dioxomorpholin-2-ylidene)ethyl acetate, C15H15N1O5
- The crystal structure of poly[diaqua-(μ2-1,2,4,5-tetrakis(1,2,4-triazol-1-ylmethyl)-benzene-κ2N:N′)-bis(μ3-terephthalato-κ3O:O′:O′′)dicadmium(II)], C17H15N6O5Cd
- Crystal structure of (E)-N′-(1-(5-chloro-2-hydroxyphenyl) ethylidene)thiophene-2-carbohydrazide, C13H11ClN2O2S
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylato-k2 N,O)cobalt(II)]-monohydrate, C36H26N4O5Co
- Crystal structure of (E)-N′-(2-chloro-6-hydroxybenzylidene)-3-hydroxybenzo-hydrazide monohydrate, C14H13ClN2O4
- Crystal structure of 1,1′-(methylene)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2S:S)nickel(II), C42H30N14Ni2S8
- Crystal structure of 1,1′-(1,2-ethanediyl)bis(pyridin-1-ium) bis(1,2-dicyanoethene-1,2-dithiolato-κ2 S:S)nickel(II), C20H14N6NiS4
- The crystal structure of 1-methyl-1H-pyrazol-2-ium nitrate, C4H7O3N3
- The crystal structure of 4,4′-diselanediylbis(8-(hexyloxy)-3,6-dimethyl-1-(piperidin-1-yl)isoquinoline-7-carbonitrile), C46H60N6O2Se2
- The crystal structure of tris(6-methylpyridin-2-yl)phosphine selenide, C18H18N3PSe
- The crystal structure of 1,2-bis(2,4-dinitro-1H-imidazol-1-yl)ethane ─ acetone (1/1), C11H12N8O9
- Crystal structure of [diaqua[2,2′-(1,2-phenylene)bis(1H-imidazole-4-carboxylato-5-carboxy)-κ4N,N′,O,O′]nickel(II)] tetrahydrate, C16H12N4NiO10·4H2O
- The crystal structure of tris(4-methyl-1H-pyrazol-1-yl)methane, C13H16N6
- The crystal structure of 5,6-dichloro-2-(quinolin-8-yl)isoindoline-1,3-dione, C17H8Cl2N2O2
- Crystal structure of (E)-(2-methoxy-benzylidene)-(4-[1,2,4]triazol-1-yl-phenyl)-amine, C16H14N4O
- The crystal structure of (Z)-2-(4-(4-bromophenyl)thiazol-2-yl)-4-(3-hydroxybut-2-enoyl)-5-methyl -1,2-dihydro-3H-pyrazol-3-one – methanol (1/1), C18H18N3O4S
- Crystal structure of tetraaqua-tris(nitrato-κ2 O,O′) erbium(III) monohydrate, Er(NO3)3·5H2O, H10ErN3O14
- The crystal structure of 1-methyl-2-nitro-1H-imidazole 3-oxide, C4H5N3O3
- The crystal structure of 1-methyl-2-nitroimidazole, C4H5N3O2
- The crystal structure of 2-carboxyl-4-nitroimidazole monohydrate, C4H5N3O5
- Crystal structure of bis[hydrido-hexaphenylcarbodiphosphoran][tetra-trifluoromethyl-(μ-diiodo)-diplatinat]
- The crystal structure of poly[μ2-aqua- aqua-(μ3-(E)-2-(4-((2-carbamothioylhydrazineylidene)methyl)phenoxy)acetato-κ3 O:S:S)sodium(I)], C10H14N3O5SNa
- The twinned crystal structure of [4,4′-bipyridine]-1,1′-diium hexachloridostannate(IV), C10H10N2SnCl6
- The crystal structure of [(2,2′-bipyridine-k2 N,N)-bis(6-phenylpyridine-2-carboxylate-k2 N,O)copper(II)], C34H24N4O4Cu
- Crystal structure of trans-1,2-bis(pyridinium-4-yl) ethylene bis(2-carboxy-4-bromobenzoate) – water (1/4), C14H14BrNO6
- Crystal structure of poly[diaqua-(μ3-fumarato)-(μ3-maleato)-(μ4-1,2,4,5-tetrakis((1H-1,2,4-triazol-1-yl)methyl)benzene)tetracadmium(II)] dihydrate, C34H32N12O9Cd4
- Crystal structure of a second modification of Pachypodol, C18H16O7
- Crystal structure of methyl 2-(4-(2-(cyclopentyl-amino)-1-(N-(4-methoxyphenyl)-1-methyl-5-phenyl-1-H-pyrazole-3-carboxamido)-2-oxoethyl)phenyl)acetate, C34H36N4O5
- The crystal structure of catena-poly[(m2-4,4′-bipyridine-κ2 N:N)-bis(6-phenylpyridine-2-carboxylato-κ2 N,O) zinc(II)], C34H24N4O4Zn
- The crystal structure of hexaquamagnesium(II) (2,4-bis(nitroimino)-6-oxo-1,3,5-triazinane-1,3-diide), C3H15MgN7O12
- The crystal structure of 7-Bromo-2-(4-chloro-phenyl)-quinoxaline, C14H9BrClN2
- Crystal structure of methyl 4-{[4-(4-cyanobenzamido)phenyl]amino}benzofuro[2,3-d]pyrimidine-6-carboxylate, C26H17N5O4
- The crystal structure of (4SR)-7-(3,4-dichlorobenzyl)-4,8,8-trimethyl-7,8-dihydroimidazo[5,1c][1,2,4]triazine-3,6(2H,4H)-dione, C15H16Cl2N4O2
- Crystal structure of catena-poly[{μ2-3-carboxy-2,3-bis((4-methylbenzoyl)oxy)propanoato-κ2 O:O′}tris(methanol-κ1 O)lanthanum(III)], C63H63LaO27